


Dating Blind

by wannaliveindeansdimples



Series: Ana's AU's [4]
Category: Supernatural
Genre: Accidental Cuddling, Alternate Universe - Modern Setting, Anal Sex, Angst, Angst and Humor, Angst with a Happy Ending, Blind Date, Blow Jobs, Fake/Pretend Relationship, First Time Blow Jobs, Flirting, Frottage, Humor, M/M, Revenge, Sexy Times, Shower Sex, Simultaneous Orgasm
Language: English
Status: Completed
Published: 2014-11-25
Updated: 2014-11-26
Packaged: 2018-02-27 00:46:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 13
Words: 16,247
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2672630
Author URL: https://archiveofourown.org/users/wannaliveindeansdimples/pseuds/wannaliveindeansdimples
Summary: <blockquote class="userstuff">
              <p>“our asshole mutual friends set us up on a blind date and didn’t tell us it was a blind date, so instead of getting to know each other we spent the entire ‘date’ scheming against them and decided an awesome way to get back at them would be to pretend to date and then have a horrendous breakup but now that we’re two months into this charade we’re not sure what’s real and what’s fake anymore” au</p>
            </blockquote>





	1. The Set Up

**Author's Note:**

> Based on this [tumblr prompt](http://yamira.tumblr.com/post/103324372542/tickatocka-how-about-a-our-asshole-mutual). In which I was tagged by [Yamira](http://yamira.tumblr.com)  
> This is NOT a WIP, it's completely done. However, I will probably post it a couple chapters at a time until I get it all up, because I find I get more feedback that way and I'm a sadist and a comment junkie ;)

**Summary for the Chapter:**

> They meet.  
> A plot is hatched.

**Notes for the Chapter:**

> This chapter is basically to set up the prompt, so I apologize if it starts the story a little slowly.

Dean had been sitting at the table for what felt like a year. Since Sam had given him shit about not being late, he’d worried about it and ended up coming early for once. He’d been here 20 minutes already and now it was really time for them to start arriving. He hoped Sam, Jess, and their friend wouldn’t take much longer. He was starving.

He wondered about this friend they wanted him to meet. Sam said he was an analyst, which Dean really only remembered because it had the word anal in it and Dean was nothing if not a fan of dirty innuendo. He would not, as Sam had worried, make the joke to the guy. He wasn’t an orangutan.

Dean’s musings were cut short when his phone went off with a text from Sam.

**> Sorry, man, running late. Cas might beat us there. Be there ASAP, promise!**

**You jackass! After you gave me a speech about being on time?**

**Hurry up, I’m freaking hungry**

Dean rolled his eyes, then schooled his face into a polite smile as he saw the waiter coming back with the beer he’d ordered. Just as he arrived and put the napkin down, the hostess was back with a dark-haired guy in a rumpled coat.

“Here you are, sir. Sam Winchester’s table. Alec here will take your drink order when you’re ready.”

“Thank you very much,” the man said, taking a seat across from Dean with a small smile. “I suppose I will have to move whenever they arrive, but it seems a bit awkward to sit next to you right now, doesn’t?” he asked Dean, still smiling. In answer to the waiter’s question, he said, “Your best mid-grade whiskey, neat. And a glass of water? Thank you.”

Dean stuck his hand across the table, once the waiter had left. He smiled and introduced himself, “Hey, I’m Dean. It’s nice to meet you.”

“I’m Cas. Your brother and his fiancée speak very highly of you.”

Dean nodded and sipped his beer. “They say good things about you, too. What is it you do again?”

“I’m a financial analyst for the firm. I understand you’re an inventor? You brother said you created a new kind of gadget. I’m sorry, I’m not very good with machines and technology, so I don’t remember what it was called.” He smiled and thanked the waiter and raised his glass to Dean in salute before taking a sip.

“That’s cool, man. It’s a combination electro magnetic field detector and emf generator,” Dean told him with a small bit of pride.

“And, forgive my ignorance, but what is the application for either of those things?”

“Well, the detector is important for a couple of things. The most common being paranormal investigations, which are all the rage. The second is figuring out if electrical appliances and wires are giving off a field and causing residents in a home health problems.” He drank a long swallow of his beer. “As for the generator –“ His phone buzzed in his pocket. “Sorry, it’s a text from Sam, one second.”

**> Dude, no way can we make it, I’m so sorry. You and Cas go ahead and eat without us. I’ll make it up to you, I swear. **

There was an attached picture of traffic, which might have convinced anyone else, but Dean spent a lot of his time driving around. He happened to know that the picture was taken heading _away_ from the direction of this restaurant from where Sam’s office was.

“Son of a bitch!” Dean said, realizing right away what had happened.

“I take it you have drawn the same conclusion from your text from Sam as I did from my text from Jess,” Cas said, scowling slightly.

Dean nodded, lips pursed. “What gave _her_ away?”

“They’ve apparently forgotten that I work in the same office. I know they’re driving in the opposite direction of this restaurant.”

“ _Right_? Like they think we don’t know this town,” Dean said, mildly offended that his brother and Jess thought so little of his intelligence and their friend’s.

Cas made a face and shook his head in annoyance. “I’ve told them that I’m not interesting in dating. I can’t believe they tried this!” He groaned in disgust.

“Same here, man, you are preaching to the choir. I am gonna get them for this,” he vowed as he finished his beer, staring into space. Then, realizing how it might sound, he added, “I mean, look, I’m sure you’re a nice guy and all –“

“No, please, Dean. Don’t apologize. I’m sure you are very nice, too, but as I said – not interested in dating and hate set-up dates with a passion.” He downed the remainder of his whiskey in one gulp, shivering slightly. “I do like the idea of getting back at them, though.”

Dean caught the waiter’s eyes and snapped, pointing down at their drinks. Alec smiled and nodded, holding up a finger.

“Right? They need to pay for this. I mean, how old are they, seriously?” he asked with an incredulous shake of his head.

“You know,” Cas leaned down conspiratorially and then jerked back slightly, as if unsure about what he was about to say. “Nothing, never mind,” he said.

The waiter was there with their drinks then. “Would you like an appetizer while you wait for the rest of your party?”

“Uh, actually, we’re it. Can you give us another minute?” he asked with a smile.

“Certainly, sir. I’ll be back shortly.”

“Listen, Cas, we may as well eat, since we’re here. We can hatch revenge plots better on a full stomach, right?” And he could spend some time examining how hot the guy was, now that the whole “Sam’s-friend-off-limits” blindfold was gone.

“All right. If you’re sure you don’t mind. I am rather hungry,” he confessed, picking up the menu.

“Me, too.”

When the waiter came back, they placed their orders and then Dean asked, “Ok, so what were you going to suggest earlier? Don’t hold back here, let’s brainstorm.”

“Well, I was thinking, we could pretend that we turned this into a date and then it ended badly. For instance, we could tell them we slept together and then I left before you woke up and never called you again. If you acted very excited –“

“Nah,” Dean said as he swallowed more beer and shook his head. “That’d never work. For one thing, they’d never believe you were the one who didn’t call _me_ –“

“You don’t know me! I could be a notorious lothario –“ He was stopped by Dean’s raised eyebrow. “All right, fine, so we say you left and didn’t call me?”

Dean pursed his lips, considering, but shook his head no again. “No good. That’ll just make them mad at me. Then it won’t be revenge, it’ll just be more crap than I’ll get for saying we left without a date.” He quickly finished his second beer and signaled for another.

Cas signaled for a third whiskey as well, then finished his current one in one go. “All right, well, what do you suggest? I mean, we could tell them we didn’t get along, but I doubt they would believe it. They must have been rather certain of our compatibility for them to feel confident in this ruse.” He laughed slightly and Dean noticed the apples of his cheeks were slightly rosy. “No doubt they thought we’d be too lost in each other by the time their texts came for us to notice the direction they were heading. Which, I must say, doesn’t make me feel good about their opinion of me.”

“I know, right? Like I would mack on my brother’s friend like that. Or you’d hit on your friend’s brother.” He smiled and thanked Alec as new drinks were placed before them. He was already feeling a little buzzed, probably because he’d skipped lunch working on a project. “I don’t know, man, but we gotta get ‘em, right?” He considered as he sipped his beer. “Ooh! Now, one date ending badly won’t really work, but what if we convinced them – nah, forget it. That’s too much.”

“No, please. As you said, we are brainstorming. If it doesn’t work, perhaps it will make me think of something else that will.”

“Ok, well, I was thinking, what if we pretended to start dating, like as in dates, _plural_ , huh? We convince them their little ruse worked, tell them we’re going out - and then we have a spectacular break up! We both get to act mad at them for setting us up with the lying bastard who broke our hearts? It’s perfect!”

Cas chewed his lip and Dean barely thought it was sexy at all. “Hm, that’s not a bad idea, actually. The one hiccup I foresee is that, knowing Jess and Sam as I do, I suspect, if they believe we are together, that they will want to double date.”

Dean nodded, thoughtfully. “Oh, yeah, they are totally the gloating type, who’d wanna see their matchmaking at work, huh? Well, I mean, we can fake it, right? I know my brother, we’ll end up bowling. Hard to be openly gay in a bowling alley, so it’s not like we’d have to put on a big show or anything.”

Cas sipped his whiskey and stared at Dean, a smile breaking over his features. “This is a perfect plan.” He raised his glass toward Dean in a toast. “To revenge,” he said.

Dean clinked him and joined him in a grin.

**Notes for the Chapter:**

> Thanks for reading, darlings ♥ You know I love you, right?


	2. The 1st Not Date

**Summary for the Chapter:**

> They get together for a planning meeting.

**Notes for the Chapter:**

> Ok, once these are posted, I'll probably post two more tomorrow and then not post again until Friday since it's Thanksgiving here and I'll be gone all day Thursday.

At the end of Jess and Sam’s foiled attempt at a forced date, Dean and Cas had exchanged phone numbers and agreed to get together to hash out details. As they’d eaten, they’d figured out how to convince Sam and Jess that their plan had worked. In the end, they had settled on pretending not to realize it was a set up. Dean had sent Jess a text, asking if she minded if he went out with her friend and Cas sent Sam the May-I-date-your-brother equivalent.

True to expectations, once Cas and Dean had pretended to go out a few times, Sam and Jess had quickly invited them to have a double date night. Apparently realizing that he did not know enough about Cas to fake it the way they’d talked about, he called Cas and invited him to dinner.

“If we are going to convince them, we need to actually learn some stuff about each other, so I figure we can talk over dinner and strategize,” he explained.

“That’s probably a good idea, Dean,” Cas agreed. “When would you like to meet?”

“Well, actually, are you free tonight? I’ve got meetings with west coast and Hawaii people the rest of the week, but I’m hungry and available right now,” he said with a laugh. “I know it’s short notice, but they were wanting to get together Friday, so…”

Cas smiled. It was certainly no hardship to stare across at the handsome older Winchester instead of down at the frozen dinner he’d been planning to have. “Tonight is good. How do burgers sound?”

Dean joked, “This isn’t a real date, Cas, you don’t have to impress me.” Cas assumed it was a joke about the simplicity of the food, until Dean followed up with, “As Sam and Jess will expect you to know, burgers are my favorite food, man. Better than steak, pizza, whatever. Just give me a really good burger and I’m a happy man.”

Cas was surprised and a little unnerved. “Well, as Jess is happy to scold me about – and will no doubt expect you to know about me – I feel the exact same way. I find burgers…comforting.”

There was a smile in Dean’s voice as he proclaimed, “You’re all right, Cas. You got somewhere in mind?”

Cas named his favorite place to get a burger and Dean laughed.

“I friggin’ love that place.” Cas was treated to a breathy chuckle. “You know? If I have to be stuck fake-dating anyone, Cas, I’m kinda glad it’s you. See you in half an hour?”

“Yes, Dean, see you there.”

An hour later, they were enjoying burgers and exchanging information. It felt so easy and natural that Cas forgot sometimes that it wasn’t actually a date. Dean, however, was always quick to remind them both, frequently bringing the words “fake date” or “revenge plot” into the conversation, as if he could sense Cas’ thoughts.

Cas was grateful, since he certainly wasn’t looking to date and didn’t need the complications that would arise from getting confused about where they stood. However, as they were walking back to their cars at the end of a long, enjoyable evening, Cas was struck by two thoughts almost simultaneously.

The first thought was that, were this a real date, he’d almost certainly have his tongue sliding into Dean’s perfect bow of a mouth right now. On the heels of that thought was the realization that the pair of them would almost certainly be expected to kiss on their double date. It wouldn’t do to have a fumbling, awkward first kiss in front of Sam and Jess where it was sure to give them away.

“We should kiss,” Cas blurted. He felt his face burn as Dean’s eyes grew huge in shock. “I mean,” he hastened to explain, “Before we meet with your brother and Jess. We should kiss before that so it’s less awkward when we do it in front of them.”

Dean pursed his very soft-looking lips and slowly nodded. “You’re right. I’m glad you thought of it. Sam will expect me to be affectionate with you. Good thinking.” He cleared his throat. “So, um, here or you wanna do it some place more private, like, I don’t know, inside my car?”

Cas looked around at the crowd of people milling about the parking lot. “Probably the car?” He didn’t really mind public displays, but he felt like this should be private, for some reason. A first kiss – even a fake one – should be private.

A minute later, they were seated in the front seat of Dean’s big black car, the smell of leather and Dean tickling Cas’ nostrils pleasantly. “I like this car,” he said, only stalling a little bit. He genuinely did like the vehicle.

“Yeah? She’s my baby. Restored her myself.”

Cas nodded, stroking the leather seat. “She’s very nice,” he told Dean with a smile. Then he squared his shoulders and cleared his throat. “Ok, shall we?”

Without answering, Dean scooted closer and leaned forward, tilting his head just so. He kept his hands to the sides, but Cas saw them twitch, as though Dean was having to fight not to touch. It gave Cas a small thrill to note that, but it was short-lived. Soon those shiny, rosy lips were pressed against his own and his brain shorted out.

It seemed his entire body reacted to the touch. While he was pretty sure later that he had not _actually_ arched every part of himself toward Dean, it was certainly a desire that every part of him seemed to have. _ClosercloserDeanDeanCloser._ The mild attraction he’d been battling had turned into full scale want now and there was no going back.

Well. This certainly complicated things, he thought as soon as his brain was functioning again. That didn’t happen until Dean broke the kiss to take a long, hitching breath.

“Um,” Dean summed up nicely.

“Mm,” Cas agreed.

“We should, uh…” But Dean seemed at a loss as to what they should do. Go their separate ways before it got any more awkward? Go to Dean’s and get it out of their system? Call off this whole revenge plot?

Cas broke the stalemate by opening his door. He hadn’t even known he was going to do it until the cool night air was washing over his heated skin. “Call me or text me if you think of anything else you think I should know about you before the double date on Friday, ok?” He hesitated then truthfully added, “I had fun tonight.” He walked to his own car without looking back or waiting for an answer.

**Notes for the Chapter:**

> *schmoops your faces* And what did you lovelies think of the kiss, hm? ♥


	3. Fake Doubles

**Summary for the Chapter:**

> Dean and Cas have their double date with Sam and Jess. It holds a lot of surprises for Dean.

**Notes for the Chapter:**

> This chapter is 99% fluffy, flirty fun.

Dean was definitely looking forward to tonight because they’d be pulling one over on Sam and Jess – and only a little bit because he got to kiss Cas again and because Cas was fun to hang out with.  There was definitely not a super-secret part of his brain that wished they’d gone along with Sam and Jess’ plan of hooking them up. He wasn’t looking to date and Jess and Sam’s trick had been sneaky and underhanded and they needed to pay. They couldn’t toy around with people’s lives like that.

He got dressed up just like it was an actual date and even put on his best cologne. Sam would know it wasn’t real if he didn’t act like he was trying. He and Cas had agreed that he would pick Cas up at his apartment and that’s where he headed once he was ready to go.

“Hey, man, you ready for this?” he asked as Cas slid inside the car.

“I think so. We covered all the basic information I think people who’d been dating a couple of weeks would know.” Cas turned to look out the window as Dean pulled back onto the street, so Dean almost didn’t hear him say, “And we don’t have to fake an attraction to each other.”

Dean cleared his throat nervously. “No, uh, that’s all true. Cool, so I guess we’re good to go. Um, about the plan, how long do you think we should keep up the dating thing? A month?”

Cas turned back toward him, mouth twisted in thought. “Hm, I wonder if a month is long enough. I hardly think either of us would get our hearts broken in so short a time. Two months is pushing it, but it’s more plausible, I think.”

Dean nodded slowly as he navigated a turn. “No, I could see two months. We wouldn’t have to sell full-on ‘in love’ that way. We could just say we’d been starting to fall for each other, you know?”

“Yes, I think that’s a good idea. Any idea how you want to handle the inevitable break-up?” Cas asked, checking his nails.

“No, not yet. I’m sure we’ll come up with something, though, right?” Dean asked as they pulled onto a main highway.

“It’s a shame they changed their minds about bowling,” Cas said after a few beats of silence.

“Yeah, I can hardly believe that. Sam’s usually so predictable. Of course, it’s been a really long time since I went on a double date with them, so…” He shrugged. “Anyway, like you said, not like we have to fake attraction, so that helps, I guess. Although, to be honest, our attraction may actually complicate things.”

“You mean because we will actually enjoy all the touching and get…worked up, as it were,” Cas surmised.

“Well, yeah, something like that,” Dean agreed.

To his complete surprise, Cas said, “You know, Dean, we are both adults and I am certain you have had your share of sex without strings. I see no reason why we could not navigate such a scenario in this situation.”

Dean laughed. “Are you saying that there’s a chance I might get lucky on a fake date, Cas?”

Cas smiled back. “That is exactly what I’m saying, Dean.”

Dean was looking more forward to the evening than ever. When they pulled to a stop at the restaurant, Dean could see Sam and Jess watching them. Without making eye contact with his brother, Dean looked over and pretended to notice a problem with Cas’ collar.

He put a smile on his face and slid his hands up to fiddle with Cas’ shirt. “Here let me fix that for you,” he murmured before dropping his face so that Sam couldn’t see his mouth. “They’re watching us right now,” he explained.

Cas smiled down at him and covered Dean’s hand with his own. “Thank you, Dean.”

Dean pressed a quick kiss on the end of Cas’ nose and hastily pulled away to get out of the car. He walked around to Cas’ side and offered him a hand out, but Cas declined. When he stood up, Dean slid an arm around his waist and Cas briefly lay his head over on Dean’s shoulder.

“Well, look at you two!” Jess exclaimed, clearly pleased. She and Sam shared a smug look and so did Cas and Dean – though the latter couple’s was more a shared smug eye roll.

“I’m starving, let’s eat!” Dean said, breaking the moment.

Dinner was easy and fun, Cas and Dean having prepped each other well. Sam and Jess mostly carried the conversation, but they kept dragging Dean and Cas in, too. There was a host of “So, Cas, did Dean tell you about the time…” and “Hey, Dean, did you know that Cas…” and similar gambits. For the most part, Dean and Cas were able to shut them down, since they had indeed exchanged the information.

Once or twice, however, one or the other was surprised by the story and Dean had to admit he enjoyed the things he was learning about Cas. He thought maybe they could stay friends when this was all over and that was a pretty cool thing, in Dean’s book. Cas seemed like a pretty cool guy.

After dinner, Sam suggested they see a movie. Dean said he’d love to, taking Cas’ hand and leaning in close to say, “It’s been years since I made out in a movie theater, how about you?” He waggled his eyebrows for effect and Cas batted him away, smiling.

“What happened to taking it slow?” he asked Dean with a cocked brow of his own.

“Hey,” Dean said with a laugh, “For me, two weeks _is_ taking it slow.” He winked and Cas rolled his eyes, still smiling.

“Wow, Cas, he isn’t kidding. He must really like you,” Jess said, half-jokingly.

“Shut up,” Dean said, faking blustery embarrassment because it was expected.

“Well, I don’t know about _that_ ,” Cas said, smiling. “But he knows about my, um, my…situation,” Cas told her with a meaningful look at Dean, “And he’s been very understanding.”

Dean played along and gave him a knowing nod - as was the point of Cas’ look - so it seemed like Dean actually knew what the hell Cas meant. However, he most definitely did _not_ know and now he wanted to. He’d have to ask Cas on the way to the movie theater.

“So, we ready to divvy up here and head to the movies?”

“Actually, Dean, why don’t you let us get this one? It’s the least we can do after you got stuck with the check last time,” Sam offered.

“Sure thing, Sammy! I’m not gonna turn down a free meal, are you, Cas?”

“No, Dean. We thank you, Sam, that’s very generous.” And a nice extra bit of payback, Dean thought, since they’d both had pricey meals and more than one drink each.

“Meet you at Gallery 12?” he asked Sam, standing up and holding out a hand for Cas.

“Yeah, see you in a few.”

“Ok, so,” Dean said as soon as they were safely inside the car. “What’s this situation I’m supposed to know about?”

Cas’ eyes went wide and he fidgeted nervously, buckling his seatbelt and avoiding the question for as long as possible. “It’s nothing. Don’t worry about it.”

“Come on, man, you brought it up. What if I do something that doesn’t jibe with what Jess knows? It’ll be a dead giveaway or it’ll make me look like an ass.”

Cas sighed and nodded. “You’re right. I just…ok, the thing is, I haven’t…in a very long time and the last time, well, it wasn’t a good experience, all right?”

“Oh,” Dean said. Then he smirked slightly. “So when you say you don’t date, you mean it _isn’t_ because you’re a notorious lothario?”

Cas huffed a laugh and smacked his arm. “Assbutt,” he complained.

Dean smiled and started the car. “Yeah, that’s me.” He turned to Cas with another eyebrow wiggle as they waited for traffic to clear so they could pull out. “We still get to make out, though, right?”

Cas rolled his eyes, but Dean could see that he was smiling behind his hand.

**Notes for the Chapter:**

> *quietly reaches over and holds your hand* *whispers "I like you"* ♥


	4. Fake date, Actual Lucky

**Summary for the Chapter:**

> Making out in the theater leads to more making out.

**Notes for the Chapter:**

> Consider this pre-smut, I guess you'd say. Hm, I may have to rethink this two chapters thing. If I leave it here, you might form a mob...

Less than two hours later, Cas found himself standing in the middle of Dean’s living room. He shook equally from nerves and desire. Dean was in the kitchen, getting them some alcohol. After a moment, Cas decided to sit on the couch. He perched at the edge, then realized he probably looked like he might flee at any time. He took a deep breath and slid back, relaxing against the cushions and trying to look like he’d ever had a casual one night stand before.

_The movie had been both a blessing and a curse. It offered the opportunity to take the focus off of them, but it also meant that Dean had to keep up appearances of following through on his tease to make-out in the theater. The fact that it was obviously annoying to Sam – he asked Dean to stop at least twice - certainly must have been a bonus to Dean, so Cas was unsurprised that Dean threw himself into it with such gusto after Sam's first unhappy complaint._

_Cas had been gone by the end of the first kiss, hard in his jeans and panting from want. He was barely aware that there was a movie happening or a theater full of people around them. He was all sensation and no thought. He let Dean’s hands wander where they wanted and his own went wherever the mood took them, as well._

_Some time in the middle of the movie, Sam suggested in disgust that they get a room and Dean had willingly agreed that leaving was a great plan. Cas, still lost in the tingle of lips, the caress of hands, and the pleasant ache of his erection, just mindlessly followed where he was led. They were already back to the car before he came back to himself enough to question the wisdom of the situation._

_Thankfully, Dean was aware of himself more than Cas. He stepped close as he unlocked Cas’ door. “Look, we got kind of carried away in there, so if you want to opt out, you just have to say. Me, I’m happy to drive you back to my house and fuck you stupid, but I can just as easily drive you back to your place and let you out without another touch.”_

_He walked around the car without waiting for an answer. He waited until they were both inside and buckled up before he turned to Cas and asked, “So, what’s it gonna be?”_

_Cas opened his mouth, then closed it again. Dean’s eyes tracked it when Cas’ licked his lips nervously and Cas felt the gaze like a touch. “Your house,” he answered hoarsely. Dean’s slow, sultry smile was a reward all on its own._

Dean returned with two tumblers filled a third of the way with amber liquid. He handed one to Cas, saying, “If you’re drinking that just so you can go through with this, don’t. We don’t have to do this.”

“Why are you so convinced I don’t want this?” Cas asked, hiding his nerves with a sip of the whiskey.

“Dude, you called it a “situation.” I’ve had enough time to figure out that there’s probably more to the story than you told me.” He sipped his own whiskey calmly, without breaking eye contact. “Then there’s the fact that your eyes have a lot in common with a skittish horse’s right now.”

Cas blew out a breath and relaxed shoulders he hadn’t realized were so tense. “It…was a situation. It isn’t now. And I do want this.” He downed the rest of his whiskey. “This,” he gestured with his glass before setting it down. “Is not to get through this. It’s to shut up the nerves that are hangovers from a different time. So how about you finish yours already so I can kiss you again?”

Dean apparently had no more to say on the issue because he quickly set his whiskey aside and pulled Cas to him. Dean suckled lightly at his bottom lip before he pulled out of the kiss.

“Fuck, your lips are just so…” He growled and gave it another sucking bite. “They’re fucking perfect, is what they are. Plump and soft and designed to drive a guy out of his mind thinking filthy thoughts about them.” Every couple of words was punctuated with more kisses.

“Oh, like your lips are any better?” Cas asked in a breathless whisper. “Fuck,” he agreed as he dove back in, sliding his tongue inside Dean’s mouth to shut them both up.

Dean’s tongue slid against his in sweet caress. Then Dean’s hands dropped from his head to his shoulders and then one of them made its way down to Cas’ hip, where Dean’s long fingers curled and dug in slightly. Dean firmly kneaded the top of Cas’ ass and his palm rocked against Cas’ hipbone.

That insane mouth worked magic on and in his own, losing him to all thoughts for a while. The next time he came back to reality was when Dean’s hands were pushing his shirt up towards his shoulders. Cas’ raised his arms and allowed Dean to pull it off him. He moved to help Dean, but the other man was already moving to tug his over his head.

They pressed their bare chests together, the heat like heaven, and resumed kissing. Now that they were closer, their jeans-bound erections brushed against each other and Cas let out an involuntary moan at the sudden sensation.

Dean seemed to want to hear it again because he immediately reached between them to rub his palm over Cas’ length through the denim.

“Oh, fuck,” Cas breathed. “Please, Dean, we need to be naked now,” he begged as that palm tried to drive him out of his mind.

Dean grabbed his hips and ground their cocks together a couple of times before he pushed away and started kicking off his shoes, staring Cas straight in the eye as he did so. They quickly shed their shoes, pants and underwear, both stopping to drink in the sight before them for a moment before they fell together once more, Dean’s finger burying themselves in Cas’ hair and Cas’ hands clutching at Dean’s hips.

Cas shuddered every time the heads of their cocks brushed together. After a few times, he pulled Dean closer, so that they could rut with more purpose. Dean turned and started walking them backwards.

“Where are we going?” Cas managed to break away and ask, not stopping his feet from following Dean’s.

“Bedroom. Come on,” Dean answered and then closed their mouths together again.

**Notes for the Chapter:**

> *eyes torch-laden villagers warily* *gulps* I love you? ♥


	5. Really Lucky

**Summary for the Chapter:**

> Making out leads to more than making out.

**Notes for the Chapter:**

> I totally caved to my fear of pitchforks and decided to give you a third chapter. I know, I know, I'm awesome like that. ;)  
> No more pre-smut, folks. This is the real deal. If you wish to maintain the purity of your virgin eyes, turn away now.

Dean had already made a decision about how they were going to do this by the time he’d taken off his pants. He hoped Cas would be on board with it and he couldn’t see why he wouldn’t be. Still, as he carefully walked them back toward the bedroom, his heart thrummed in excitement. This was the hottest make-out session he’d had in…shit, he wasn’t sure. It had been a long time.

Finally they were in the room and he turned them so that Cas had his back to the bed before he gently lowered him onto it. He got them onto the bed, his legs between Cas’, their cocks almost perfectly aligned. They kissed and slid rocked together like that for several minutes before he fumbled in the night stand drawer. It had been a while, so it took a minute to find the bottle of lube, but finally his fingers closed over it.

It was good lube, but the bottle design left a lot to be desired, as there was no opening it one handed. He groaned as he pulled out of the kiss. Cas continued watching his face and did not stop the rocking of his hips. Light sparked behind Dean’s eyes as Cas’ head slid against his own. Then Cas reached down and cupped his balls, squeezing just enough to make Dean gasp in pleasure.

Still, Dean managed to lube up one hand and get it between them. He spread the cool gel between both their cocks and locked his fist around them. Then he fucked up into his hand and Cas did the same, the pair of them locking eyes. Dean adjusted the angle so that the hand Cas was cupping around Dean’s balls pressed against Cas’ own.

He saw those blue eyes widen and he smiled victoriously. Cas responded by kneading just a bit more and Dean bit his lip to hold back a gasp. When he saw Cas’ smirk he bent down to lick it off him. Cas’ tongue was an evil thing, making him want to open himself to it forever and do nothing else.

He wasn’t allowing himself to think of whether they’d get a next time – he never got a next time – so he shut down his brief regret that he hadn’t gotten to feel that tongue on his cock. Instead, he concentrated on all the glorious sensations coursing through his body at this moment. His pleasure mounted and gathered, his balls drawing up and his breath coming in ragged pants.

He pulled back and looked down at Cas to see if he was similarly close. His blown out pupils and slack mouth said he was. “Dean,” he whispered and it snapped the fine wire that had been holding Dean back.

With a full body jerk and a repeated cry of nonsense syllables, he came, hard, spilling onto them both. Cas moaned and came as well, their seed mixing together on their hands, cocks and stomachs.

Dean collapsed forward, laying his head on Cas’ shoulder. “Fuck, Cas,” he murmured. They lay there, absently petting one another, as the aftershocks passed. Then Dean carefully pulled himself off of the dark-haired man and made his way to the bathroom for a wet towel.

He was on shaky legs as he stood in front of the sink. He stared at his reflection in the mirror and saw that he looked completely wrecked. He couldn’t believe how hard he’d come. That was the best sex he’d had in a long while, no question, but even so his continued shakiness surprised him.

Once the water was warm and the towel wet, he made his way back to Cas, who had dozed off on the bed. Dean was struck by the urge to kiss him awake, and he almost resisted it. The point of this had been to get it out of their systems, after all. On the other hand, since he wouldn’t get the chance to taste that mouth again, he might as well take it while he could, right?

So thinking, he leaned over and pressed his mouth to Cas’, slipping his tongue inside as soon as those amazing lips parted slightly.

“Mmm,” Cas moaned into his mouth. When his hands came up to card into Dean’s hair, Dean pulled back and started cleaning them up.

"I have a question," Cas asked as Dean finished and prepared to toss the towel in the hamper. 

Dean looked at him and then threw the towel. "Sure, go ahead."

Cas stretched in a way that should not have Dean's 30 yr old cock twitching like he hadn't just had an orgasm. "Does one night stand mean you are limited to a single instance during that one night?"

Dean paused on his way to grabbing his pants off the floor and cocked an eyebrow at Cas. "Any particular reason you're asking?" he managed to ask softly. 

In lieu of speaking, Cas raked his eyes over Dean from head to toe as Dean slowly stood back up. Cas licked his lips and nodded. Dean was back on the bed in an instant, kissing that mouth again, for all he was worth. His cock informed him age was just a number and sprang to life once more, in record time. Dean didn't even question it. 

Cas pulled out of the kiss and gasped, "Maybe a shower? I'd really like you in my mouth, but I don't particularly like the taste of lube." He grinned and dove back into the kiss before Dean could respond. 

Without breaking their lip lock, Dean hoisted Cas in the air and carried him to the bathroom. No sooner did Dean have the water warm than Cas was tugging him into the tub. He grabbed the soap from behind Dean and started lathering him up, moving quickly from Dean’s sparse chest hair down to the thick blonde thatch of curls below his navel.

Then a soapy hand grasped Dean firmly by the cock and started gently lathering it up. Cas’ other hand, also soapy, slipped down to his balls, giving them a good lather before dipping further back. The hand on Dean’s cock didn’t slow, even as Cas’ fingers slipped over his hole and took his breath.

He found himself pushed backward under the spray and Cas thoroughly rinsed him before pulling him forward. Once the water was once more pounding against his back, Cas dropped to his knees, teeth closing around a hipbone briefly. Then that hot mouth sucked him down and Dean began babbling.

“Oh, fuck, Cas, yeah. Suck it just like – oh, shit, yeah, take it all, fuck!” He stroked a wet hand through Cas’ thick, dark hair and held on gently. “Fuck, those lips look even better on my cock than I imagined. Ah, fuck! Yes…they feel better, too.” Dean had no chance to hold out against Cas’ obvious skill, especially since his hands had returned to their earlier explorations. “Yeah, Cas, suck it, suck it, suck – _fuck, Cas!_ ” he cried out as he came over Cas’ tongue and against the back of his throat.

He was wobbly afterward, but he found the strength to yank Cas back up into a standing position and kiss the taste of himself out of his mouth. As he trailed lips and tongue and teeth against Cas’ neck and ear and shoulder a still-dazed minute or so later, he murmured, “Only person in a decade I’ve ever hoped for a round three with,” before he fully realized he was saying it.

Once he did, he chose to go for humor and innuendo to keep it from sounding so  _significant_. He grinned up at Cas from near the guy’s chest and winked. “You know your way around sucking a guy’s dick is what I’m saying,” he clarified, which was a fully truthful statement.

Cas smiled back, but there was an edge to it and he pressed down on Dean’s shoulders. “Any chance you’re going to get around to practicing your own skills before I lose my goddamn mind?” he asked and drew a genuine laugh from Dean as he dropped to his knees.

Dean took the soap from where Cas had left it and washed him up, much like Cas had done for him. Unlike Cas, however, he played around Cas’ hole a little longer, until Cas was rocking back and forth between his soapy fist and his soap-slick finger. The gasping little breaths he was taking had Dean grinning from ear to ear.

“Please, Dean,” Cas pleaded. “I’m so close,” he promised brokenly.

Dean kept up his ministrations for another minute before he finally took pity on Cas and his leaking erection. He rinsed him well and then reached back to turn off the water before it got cold. Then he took Cas’ cock, slightly longer and thinner than his own, slowly into his mouth. He spied a bottle of lube on the corner of the tub and grabbed it, slicking up a few fingers.

As he licked and sucked at Cas’ cock, paying extra attention to the dripping, swollen head, he gently reached back with his lubricated hand. He slid a fingertip over the rim a few times and Cas’ hips bucked forward, sending the guy’s cock further into his mouth. Dean very carefully inserted just the tip of his finger, and Cas pushed back onto it.

“ _Dean_ ,” Cas whispered.

Dean obliged his unspoken request, pushing his finger the rest of the way inside. He teased Cas and drew out the blow job, stretching and playing with his prostate until he had all three of his lubed up fingers inside and Cas was a sobbing, begging mess above him.

“Come for me, Cas,” Dean instructed, finally tightening his grip and speeding up his strokes, while also caressing that magic spot with his fingers.

Cas came with a shout and a series of gasps and Dean swallowed the evidence down. Then he was helping Cas as he slid down onto Dean’s lap in a boneless heap. It wasn’t the most comfortable place to cuddle, but Dean thought that was for the best. He wasn’t the cuddling type, anyway.

“Fuck, Dean,” Cas finally said. “That was…incredible.”

The sincerity in the other man’s voice and face left Dean shaken. Before he could worry too much about it, though, Cas’ expression changed into a smirk and he repeated, “You know your way around sucking a guy’s dick, is what I’m saying.”

Dean laughed and shoved him off, the moment gone. “Come on, we’d better dry off before we catch pneumonia or some shit.”

Cas just nodded and got to his feet, not looking back as he stepped out and grabbed a towel. Dean watched him dry off, still enjoying the view, despite his having just gone two rounds with the guy. As Dean dried himself off, he realized he hadn’t eaten in a while and probably needed to soon, given the energy he’d expended.

“You hungry?” he asked as he hung his towel over the rod.

“No, I’m fine,” Cas said, just as his stomach growled.

Dean laughed again and swatted him on the ass. “Come on, let’s get dressed and we’ll grab some food on the way back to your car.”

**Notes for the Chapter:**

> You didn't even try to look away, did you? ♥


	6. Future plans and sleepovers

**Summary for the Chapter:**

> They have a late night dinner and plot their next move.

**Notes for the Chapter:**

> See if you can spot my favorite line from this chapter.
> 
> *Ok, so it's Thanksgiving and I wasn't going to post today, but I was standing in my SO's sister's kitchen this morning reading all your lovely comments and smiling like an idiot, so this is my thank you gift to you, my darlings! Mwah!

Cas felt mild disappointment that there wouldn’t be a round three, after all, but he didn’t let it show. He just pulled on his clothes in silence and walked out to the car with Dean once they were both dressed.

When they were inside the car again, he said, “I really enjoyed tonight, Dean. I haven’t had sex that good –“ _Ever, Dean. I’ve never ever felt like that before._ “- in a really long time.”

“Hey, we can still skip food and run back in for a round three,” Dean joked.

Cas could see he was just a little bit serious and that made Cas feel better, at any rate. Before he could respond, though, his stomach answered for him again and Dean smiled and shook his head, starting the car without another word.

The only thing open was a diner a mile from Dean’s that specialized in breakfast all day. Cas had a soft spot for breakfast, so he indulged himself. He got the special that was basically every breakfast food that Americans ever ate - and it came out to him on four separate plates. Dean got a similar order, though his only took three plates. For some reason, Cas was pleased by that.

As they ate their fill of cholesterol, saturated fats, and ridiculous amounts of sugar, they discussed more strategy for the upcoming weeks. They had agreed to keep this up another month and a half, so they needed a good plan. Already it felt like the past couple of hours was a dream and Cas felt like he’d lost something. Which was stupid. He didn’t date. He never really had.

“What I’m thinking is, to sell it from here on out, we gotta be visible, you know?” Dean said as he took a large bite of pancakes. Once he chewed and swallowed most of it, he added, “Like, when I know I’m gonna see Sam, I’ll let you know so you can text me and vice versa. That way, they see us being…couple-y,” he said, gesturing with his fork.

“Couple-y?” Cas repeated, smirking. At Dean’s fierce look, Cas laughed and took a bite of waffle. “Ok, so we’ll text when we know the other one is with Sam or Jess. What about if they want to double up again?”

“Oh, you know they will,” Dean groused with an eye roll and a sip of coffee. “Gloaters, just like we said. We just grin and bear it like tonight, I guess.”

Cas frowned slightly, in thought. “Well, I guess what I’m asking is, how convincing do we want to be here? Because, if we were dating, we’d know all the new stuff going on with each other – like if something funny happens at work or whatever – and we’d also be making new stories to tell _them_ , you know? ‘Oh, we were at this great little place the other night, they had really good music,’ for instance.” He nibbled on a sausage link and waited for Dean to talk.

Dean squinted and pursed his lips in concentration. He nodded around a bite of eggs. “I get what you’re saying, yeah. So, what? You think maybe we need to actually get together once a week or something? They won’t actually _be_ dates, but we let them think they are?”

Cas shrugged and nodded as he finished off his coffee. “I think it makes the most sense, unless you want to do research on restaurants in the area.”

Dean shook his head no. “Nah, too much risk involved. I try to lie to Sammy about a restaurant we went to, turns out the place was closed that night for renovations and Sam hears about it. No thanks.”

“So, once a week, then?” Cas asked and then sighed heavily as exhaustion finally hit him. “I should get the rest of this to go, I suppose. Otherwise, I won’t feel up to driving by the time we make it to my car.”

“Damn, dude, I didn’t realize you were so tired.” Dean shook his head and waved a finger at Cas’ meal. “Finish your food. You can crash at my place.”

“Dean, you don’t have to –“

“Come on, man. We’re friends, right? So crash at my place. I can sleep on the couch.”

Cas rolled his eyes and gave Dean a severe look before leaning forward and lowering his voice. “I just had my dick halfway down your throat, I’m pretty sure we can share a _bed_.”

Dean choked on a surprised laugh and held up his hands in surrender. “Damn, dude, fine.” He pointed at Cas and ordered, “But no cuddling,” in a low voice.

Cas rolled his eyes again, this time so hard he thought he might have strained something. They finished their meals in silence and Dean insisted on paying. He argued logically that it would be faster and Cas could get the next one, since they were planning on getting together so often for a while. Cas was about to fall asleep at that point, so he agreed easily.

Back in Dean’s house again, they took turns in the bathroom – Cas with a spare toothbrush – then stripped down to their boxers and climbed into the rumpled bed. They said their goodnights a little awkwardly, but Cas knew on his part it was because part of him wanted to kiss Dean again before they fell asleep. The man was a phenomenal kisser, so it wasn’t that surprising.

He expected to fall right to sleep, but instead he lay awake in the dark for a while, listening to the unfamiliar house-settling sounds. He was no longer sure how interested he was in revenge, but he was glad he and Dean were friends. He was actually looking forward to getting to hang out with him over the next few weeks.

He hoped they could maintain the friendship after that, too, but he didn’t know how Dean felt about that. He had a feeling he felt the same, though. He dared not hope that they could work out a mutually beneficial agreement with regards to continuing to have sex, but it was a nice dream that lulled him, at last, to sleep.

When he woke up a few hours later with Dean wrapped around him like a sweaty octopus, he could only laugh. “You little shit,” he whispered affectionately before drifting back to sleep again.

**Notes for the Chapter:**

> Poor, Cas. I guess he was just worn out from ~~all the banging in the previous chapter~~...something. ♥


	7. Home on the range

**Summary for the Chapter:**

> It's brother bonding time.

**Notes for the Chapter:**

> Sometimes the things that come out of my head surprise me*.

**> You should smile and then glance up at Sam. See the smug, sappy look on his face? **

**> That's what he looked like for the rest of our meeting yesterday after you texted me.**

When Dean read Cas' text about Sam's smug face, his smile became genuine - which didn't help Sam's expression at all, of course. As it became more earnestly sappy, Dean laughed out loud. He shook his head and texted Cas back when Sam turned away in a huff, feeling slighted. 

**Man, you mean I have two more hours of THIS?**

Dean took a picture of himself making a caricature of Sam's face and then hit "send."

He was grinning to himself, knowing just how Cas would sound when the picture shocked a laugh out of him. He shook his head, still smiling, and shoved the phone back in his pocket. 

"Come on, Sam, don't be like that. You want me to ignore Cas when he texts me?" He knew the answer to that and it worked as intended. 

Sam turned around and said, "No, of course not. I'm happy for you and Cas. And so is Jess. I just wish I didn't feel like you two were so amused by that fact." He frowned and stared down into his coffee. "We actually care about your emotional health and I don't know what's so funny about that."

Dean was instantly flooded with guilt, as Sam had no doubt planned, but before he could apologize, his phone buzzed again. He frowned and pulled it out, then huffed a surprised laugh when he read Cas' latest text. 

**> Is he giving you the "We really care about you, I don't see what's so amusing about that" speech? It's very moving. **

**> It would be better with a score of violins, of course. **

Dean snorted. Sam glared and Dean made a face at him. "Dude, chill. Not everything is about you, geez."

"Oh, really? Then what's so funny you can't share with the class, Dean?" Sam asked angrily. 

"Dude, inside joke," he tried, but at Sam's continued deadpan expression and scowled and said, "Cas sent me a picture of his dick in a top hat, ok?" He wiped a hand down his face for effect. When Sam continued to look at him, doubtful, Dean held the phone closer and asked, "What, you wanna see?"

Sam held up his hands and shook his head. "No. No, I'm still scarred from the movies two weeks ago." He sighed, possibly - hopefully - in resignation. "Look, Dean I'm happy for you, all right? I just wanted you to know. I can’t remember the last time you had something that lasted a week, let alone a month.” He shrugged. “You deserve someone who makes you laugh like that," he admitted, turning away to wash out his coffee mug. 

Dean felt another spike of guilt, combined with a little bit of something else that he refused to recognize. He and Cas were buddies. That's all either of them wanted. The fact that they'd had sex again the night before didn't change that. 

"Thanks, man," was all Dean said on the subject. "You ready for the gun range?"

It was the one thing they did where Jess never joined them anymore. She was a far shot and she'd tagged along in the beginning to prove it, but she didn't like guns, so after the first few visits to the range, she'd opted out. Dean kind of wanted to invite Cas one time, but he wasn't sure how Sam would feel about it, since it was their thing now. Still, he should ask. If nothing else, it made his fake relationship seem more solid. 

He waited till they were in the car and halfway there. Then he turned to Sam and asked, "So, hey, I was wondering if maybe Cas could come along next time we do this? I mean, if he wants, I haven't asked or anything."

Sam flicked his eyes from the road in front of him for just long enough that Dean could see the happy surprise in them. "Dude, of course! That'd be...yeah, Dean, that'd be great." 

Sam was smiling and Dean felt that double twist of “guilt and something” slither in his stomach again, for just a second. He ruthlessly pushed it aside and concentrated on the scenery instead. 

"Great. I'll ask him then," he murmured to the window. If Sam thought his reaction was odd he didn't mention it. 

While Sam was getting them set up with a spot, he texted Cas to ask if he’d be into shooting with them the next week. He didn’t get a response by the time Sam came walking over, so he turned his phone off and slid it into his pocket. Then he picked up the gun case from beside his feet.

“Let’s do this!” he said with a cheerful grin, happy to be in the moment again, hanging out with his brother. He might be the idiot who tried to set him up against his will, but he was still Dean’s favorite person in the world.

As they often did, they engaged in a little friendly competition. Sam was not as good a shot as Dean was and never had been, but every once in a while, he’d have really good day where he was in the zone. It kept things just interesting enough that the wagers were still fun for both of them.

Today, though, Dean was victorious and he gave in to his desire to gloat just a little as they got back out to Sam’s car.

“Hell, yes! You are gonna wash the Impala in booty shorts – and I’m gonna film the whole thing for Jess!” He laughed with his whole body as he put the gun case in the back seat and climbed into the passenger side.

“Hey!” Sam exclaimed, pointing. “That was not part of the deal!”

“Oh, come on! You’re gonna deny your fiancée that magical moment? Shit, I’ll just invite her over, she can film it herself. Then I don’t actually have to _see_ it, I can just laugh knowing it’s happening,” he said with a self-satisfied grin.

“You’re a dick,” Sam opined.

Dean just agreed with a laugh and pulled out his phone, where he had a message waiting from Cas.

**> Well, I’ve never shot a gun and I thought that was a special brother bonding time thing, but if you’re sure…ok? **

“Cas is a riot, man,” Dean told Sam as he texted back that he was sure. He suddenly realized he would get to teach Cas to shoot and that had all sorts of possibilities for fun attached to it. Next week was looking very interesting, as far as Dean was concerned. As they drove to find lunch, Dean’s earlier worries were all but forgotten.

**Notes for the Chapter:**

> *Sam in booty shorts is not one of those things. ♥


	8. Target acquired

**Summary for the Chapter:**

> Cas joins them at the shooting range.

**Notes for the Chapter:**

> You know that Hollywood cliché where the two characters are pressed flush up against each other while one of them teaches the other one something and you just wanna be both of them? Yeah, there's some of that.
> 
> NOTE: Thanksgiving held the unwelcome surprise of having to interact cordially with a raging homophobe, so I am feeling lots of feels today. Please send extra comments so that I can bask in shared love of the gay, pretty please? Even if you've never said hi before, don't be shy, a simple "hi" to let me know you're reading will suffice. Much love to all my readers, whether LGBTQUIA or just allies who loves a little man on man smut. ;)

Cas still wasn’t sure what to make of Dean’s invitation to the gun range, but it didn’t really matter, since he had agreed to go – and the day had arrived. He hadn’t the faintest idea what to wear to a gun range, but he settled on a pair of old black jeans and a thick black tee. He started to change at least three times, but managed to talk himself out of it every time.

It wasn’t like this was a date. It wasn’t like he didn’t know both of these men really well by now. Dean was already well aware of his lack of gun experience. Did Cas actually think he was going to be impressed by his wardrobe choices? Why would Cas want Dean to be impressed anyway? They weren’t dating. They didn’t date in general. They were new friends who occasionally had mind-exploding sex. That was all.

“You’re an idiot,” Cas informed his reflection, as he tugged on the belt with the eye-drawing buckle. He had to admit, he looked pretty decent in the clothes, though.

When he arrived at the gun range, he was gratified by Dean’s apparent fluster over his clothes. Maybe he’d managed to impress him, after all. Even if that wasn’t something he was supposed to want, it still made him feel good to see Dean tripping over his own tongue.

“I, uh, you don’t –“ Dean stopped and cleared his throat as Sam gave him a funny look. “I’ve never seen you in casual clothes, Cas. You, um, you look good. Really good.” Cas considered the idea that Dean was putting on a show for his brother, but he really didn’t think so.

“Thank you, Dean. You don’t look bad yourself,” Cas said, making the mistake of raking his eyes over 6’2” of sex. And now they were going to go shoot guns? That wasn’t suggestive at all.

Sam cleared his throat uncomfortably. “Hey, Cas. Glad you could make it. Dean, why don’t you roll your tongue back in your mouth and go get us a spot?” Dean glared at him and stalked off without a word and Sam rolled his eyes. “Don’t mind him. I think he’s nervous. He’s never invited anyone to come out here with us before.” Sam’s smile and words made Cas feel a little guilty. “I think he likes you.”

Cas’ joking, “I should hope so, since we’ve been dating a month!” sounded false to his own ears, but Sam just laughed along.

Sam pointed the way and started walking, leaving Cas to follow. “Anyway, I’m really glad. I think you’re good for him. He…he laughs a lot more now that you’re around.” Then Sam stopped, closed his eyes and shook his head. “Sorry. I’m not trying to scare you off by being all clingy on his behalf. I’m just really excited you two like each other as much as Jess and I thought you would.”

Feeling on more even footing now that their failed ruse had been (sort of) brought into the conversation, Cas asked innocently, “Oh, did you expect us to get along?”

Sam gave a sheepish smile and lowered his voice. “Well, don’t tell Dean, but we were kinda hoping when we invited you both to dinner that night that you’d hit it off.”

Cas narrowed his eyes. “So it was a set up?”

Sam hastily backpedaled at the accusation. “What? No, no, nothing like that. We just thought if we all had dinner, you know, maybe something would click.”

“Hm,” Cas said noncommittally.

If Sam had admitted to things, he’d feel a lot more guilty right now about tricking him and Jess into believing he and Dean were a couple. As it was, since he had opted to lie again, Cas didn’t feel all that badly about it. He spotted Dean and sent him a winning smile and wave. He couldn’t wait to tell him about this latest development. He knew Dean was battling his own guilt over their pretense.

Dean had gotten them two slots, one for Sam and one for he and Cas. This was good not only because it meant Sam’s large frame would block them from the view of other patrons down the row, but also because, once Sam put on his ear protection, Cas could tell Dean about their conversation outside.

“That sneaky little shit!” Dean exclaimed once Cas had done so. He positioned Cas and started explaining gun safety and the basic mechanics of shooting the pistol. “I can’t believe he flat-out lied about it again. Underhanded, I’m telling you. Ok, hold it like this,” he said, pressed firmly against Cas’ back and wrapping his hands around Cas’ own on the gun. “Now, once we get our earmuffs on, just take a deep breath, let it out slow, and pull the trigger, mkay?”

“Yes, Dean.” He put on his ear wear, then picked up the gun again before sighing and looking over his shoulder. “Show me one more time?” he asked because he was nervous and not because he missed the feel of Dean pressed up next to him.

Dean just shook his head and smiled, stepping back up against him once more. He wrapped his hands around Cas’ again and said, “Take that breath now.” He waited for Cas to breathe in and then out and then held him a bit tighter as he pulled the trigger. The recoil was not as shocking as he’d expected, but maybe that was the effects of Dean’s proximity.

“Good, ok, this time, aim for the target while you’re breathing. I’m gonna step back here. You got this, ok?”

Cas nodded and held up the gun on his own. He sighted the way Dean had taught him, then breathed in slowly. He let it out and then squeezed his finger. The pop was louder, the kickback more pronounced, when Dean wasn’t pressed against him. However, it was not unpleasant or unbearable and he fired off another few rounds without hesitation. He only looked at where his shots were landing once he was done.

“Wow, nice, Cas, not bad at all!” Dean told him as they brought the target forward. They were nowhere near the head or heart, but they were all within the body outline and clustered together the way Dean had told him they should be. He felt a ridiculous sense of pride. “Wanna go again?” Cas nodded vigorously and Dean sent the target back out.

**Notes for the Chapter:**

> What a lovely day for shooting!  
>  ~~I really hope all these guns aren't a metaphor for a dark turn this fic is about to take~~  
>  Gorgeous weather, isn't it? ♥


	9. When you tell one lie, it leads to another

**Summary for the Chapter:**

> Dean starts to plot their breakup.

**Notes for the Chapter:**

> Around a turn, darkly.

“So I was wondering,” Dean said before chewing a few fries. “If you’ve come up with any ideas for our breakup?”

Personally, Dean hadn’t really wanted to think about it, but it was only a couple of weeks away now, if they stuck to their original schedule. They needed to come up with a plan, as little as he wanted to. He ate his burger, not wanting to look at Cas right then.

“Um, no, not really. I guess we’ve both been busy convincing Sam and Jess,” Cas suggested, apparently lifting some part of his meal to his own mouth.

Dean risked a look and saw that Cas was staring at his own food, too. The revenge aspect of this was seeming less appealing with every week that passed. Every meal that was shared and every text that was sent – not to mention every night they gave in to the insane attraction between them that never seemed to dull.

They’d been right, he reflected. It took him about 2 months to start feeling like he could fall for the guy. He should have put a stop to this the first time they’d had sex. Instead, he’d just gotten in deeper and deeper. He sighed morosely and washed his misery and his suddenly unappealing burger down with soda.

“I guess we need to figure it out soon,” Dean said without much enthusiasm. “Spectacular breakups only work as revenge when the breakups happen,” he said on a humorless laugh.

“Or we could just not break up,” Cas said quietly, causing Dean to freeze with his burger halfway to his mouth.

He looked up to find Cas staring at a fixed point and just as frozen. He slowly set his burger down and took a moment to find his voice over the hot pounding of his blood in his ears and face.

“Cas, do you…are you saying you want to date for real?” He wasn’t sure whether fear or hope was more prominent in his chest, but he suspected if Cas said yes, he’d be happy.

Instead, Cas’ eyes flew up to his, looking as stunned as he felt and Cas rushed to say, “What? No! We – I don’t date and you, you know, don’t either, I know that and I just meant, um…Sam. I mean, I feel pretty guilty about this because he’s so happy.”

Dean felt the crushing thud of disappointment against his chest, which burned with an ache he hadn’t felt in years. “Oh. Well, so…um…what, we just keep on pretending to date forever, so he doesn’t get hurt?” Dean tried to make a joke out of it, but the prickling behind his eyes was doing something to his voice.

“I – no, I just…maybe…um, just…sort of…break up quietly.” Cas shook his head vigorously. “Never mind. It’s stupid. Forget it. I’m – I have a headache coming on, excuse me.”

With that, Cas rushed to the bathroom, leaving Dean reeling at the table. Not that he should be that surprised. This was why he didn’t date, after all. Too much opportunity for getting hurt. It wasn’t as though Cas hadn’t warned him upfront, right? It had always been a lie. Dean was the idiot who’d fallen for it. For Cas.

Knowing that a breakup was even more necessary now, Dean hatched a plan while he waited to see if Cas would come back out. He thought he knew exactly what sort of thing would be convincing enough for Sam and Jess. He pushed away the rest of his meal and finished off his drink, signaling for the check.

When Cas came back out, Dean was more composed and Cas seemed to be as well. He had obviously splashed his face because water droplets still clung to his hair. Dean blocked out all thoughts of how vulnerable he looked and concentrated on the task at hand.

“You feeling better?” he asked, knowing he sounded cold and uncaring, but not really sure how else to sound. Cas nodded, looking nervous. “Cool, so I had an idea while you were gone. For the breakup. I don’t think the quiet way is really gonna work. They’d just keep after both of us to explain what happened if we try that.”

“So, what do you suggest?” Cas asked and Dean ignored how bad he sounded. His head must really be hurting – or he was really sorry he’d said what he did and was worried Dean was angry about it. Either way, it was irrelevant to the current situation.

“It’s simple. We pretend that I got drunk and slept with someone else. A woman, probably because that’ll make it look like I’m having some big gay panic and give you more reason to not want to forgive me, should I ask for forgiveness.” Dean smiled in a way that did not reach his eyes. “Which I obviously won’t.”

“You really think they will believe you capable of something like that? Sam has talked many times of your loyalty,” Cas said, playing with the straw on his drink.

“Oh, they’ll believe it, don’t worry,” Dean assured him with another cold smile.

“How can you be so sure?”

“Because I’ve done it before,” he explained without looking at Cas. “Thanks, darlin’,” Dean said, winking at the pretty young waitress as she set the check down. He pulled bills from his wallet and threw them down before standing up. “I’ll see you, Cas,” he said as he started to walk out.

“Wait!” Cas called when he was halfway to the door.

“Yeah?” he asked without coming any closer.

Cas sighed and got up to follow him. When he caught up, he asked, “Are you angry with me?”

Cas looked so much like a lost kid that Dean’s anger dried up. What did he have to be angry about, really? The guy wasn’t into him as more than a friend and fuck-buddy. He hadn’t led him on. Dean was hurt and that was a different thing. Still, it was easier to be pissed off…but another look at Cas, still staring at him like he’d kicked his puppy, and Dean let it go.

“No, Cas. I’m not mad, man. Just, uh…you know, dredging up some stuff here,” he said, half-truthfully. He knew Cas would think he meant the cheating on an ex part.

“Of course, Dean, I should have realized. So we’re still friends?” Cas asked with a tentative smile.

Dean returned the smile and it was almost genuine this time. “Yeah, Cas. Still friends. I’ll, uh, text you tomorrow or the next day, ok? We’ll talk about a timeline for this.”

Cas relaxed a little more, his smiling growing. “Ok. Good. That’s good.” He reached out and patted Dean on the arm, in an awkward approximation of the way Dean sometimes clapped him on the bicep.

It was so off the mark that Dean had to laugh. “Nice try, Cas. I assume you were trying for this,” he said with a smirk. He slapped Cas’ upper arm a couple of times and then squeezed it briefly and let go. “Tomorrow, ok?”

He walked out before Cas could stop him again. All the way home he wondered what he was supposed to do. If this were a real relationship, he could call Sam, but it wasn’t, so he couldn’t. He could go out to the bar and drown his misery, maybe pick up someone to pass the time with, but he’d inevitably just compare them to Cas and find them lacking. It’d only been a couple of days since they’d last hooked up, so it was fresh in his mind.

In the end, he made do with drinking all the beer in his fridge and passing out on the couch watching Game of Thrones. He woke up with a crick in his neck and a hellacious headache, but at least Cas was the last thing on his mind when he made his way to his empty bed.

**Notes for the Chapter:**

> Oh, Cas...  
>  ♥


	10. Self awareness

**Summary for the Chapter:**

> Together they devise the final breakup plan, though Cas feels like he's just along for the ride.

**Notes for the Chapter:**

> The ~~Pain~~ saga continues...

Cas was lying in bed, wide awake and dreading his next exchange with Dean. He had blurted out how he really felt and then he’d panicked. He hadn’t meant to say those thoughts out loud. He hadn’t mean to give voice to the idea that he didn’t think they should break up at all.

Because, of course, despite how it felt sometimes, they weren’t really dating. Despite the fact that he sometimes woke up in Dean’s bed, with their legs tangled and a warm glow in his chest, Dean wasn’t his boyfriend. None of this was real. It never had been. While Cas was not the notorious lothario he’d joked about being, from what he’d heard, Dean was. Cas knew all of that - and he hadn’t meant to say anything.

But he had said it. And he had seen the look on Dean’s face when he’d said it. It had looked like abject horror, possibly with a side of revulsion. So Cas had panicked and deflected and then…then it had looked like maybe what was flickering on Dean’s face was disappointment. He had acted almost _hurt_ afterward.

So now Cas was lying awake, wondering whether or not he’d read the whole situation wrong. Dean had seemed so angry with him for a few minutes. Why had that been? He had analyzed and picked apart the entire evening and convinced himself completely on both sides of the issue half a dozen times.

_Yes, Dean had definitely been horrified. No, Dean had been hurt. No, Dean did not want strings. Yes, Dean wanted to be more than pretend boyfriends. No, he was only doing this to get back at Sam and Jess. Yes, that’s how it had started, but he’d developed feelings just like Cas had._

On and on it went until Cas’ entire mind was a jumbled mess. Finally, exhausted, his body took over and forced him into an uneasy sleep, plagued by dreams of Dean. When he woke up, far too early for when he’d fallen asleep, he was tangled in the sheet and soaked in sweat. The pounding behind his eyes had only gotten worse.

A few hours later he had finally rid himself of the headache and was making himself lunch when his phone rang. He felt momentarily buoyed when he saw that it was Dean, but fear quickly smothered it – and Dean himself took any remaining hope out of him.

“Hey, Cas. I was thinking. I mean, do we really need to wait another week? Why don’t we just move ahead with the whole breaking up thing tomorrow when you go back to work?”

Cas was at a loss, so all he could get out was a broken, “Why?” that he hoped didn’t sound as desperate as he felt.

“Well, I mean, we’ve kinda drug it out, right? And we’ve got the plan now, so I think the sooner we get this over with the better.” Cas heard a scratching noise and then Dean continued. “And also, you know, it occurred to me, I’ve probably been cramping your style, right? I mean, you don’t do this, so having me around all the time has probably cut into your, uh, potential for hook-ups, I guess.”

“Dean, I don’t –“ Cas heard all the possible endings in his head: _\- want to lose you. - date because I’m scared to get hurt because I was hurt before. -  do casual flings, either. – want this to end yet._ Instead, he just ended the phrase with a sigh. “No, you’re probably right. We should end it now rather than later. How do you want to do it?”

“I was thinking I’d drop by your office tomorrow afternoon about one. Sam said your bosses only work half days on Mondays, right? They leave at noon?” His voice was different and Cas couldn’t pin down how.

“Um, yes. They leave at noon. What will you do once you get there?”

“I figure you should be like coming from the break room or headed there or have some other reason to be out in front. I’ll say something about you avoiding me and then you’ll shush me and make me head to your office, but I’ll yell a little bit more before we get the door closed. Then after a few minutes behind closed doors, I storm out in an angry huff and you tell Sam we won’t be seeing each other again.” Dean paused for breath. “Sound good?”

“I…suppose so.”

“Cool. So I’ll see you then. I’ll, uh, I’ll text to remind you, ok?” Dean asked and Cas finally figured out what was different.

All the warmth he’d grown used to was gone from Dean’s voice. He sounded distant and polite, like he had the night they’d met. Only worse, somehow. His friend was nowhere in evidence.

To that end, he made himself ask, “What happens afterward?”

“What do you mean?” Dean’s voice was wary or maybe it was Cas’ imagination.

“Well, I mean, we’re friends, right? We’ll keep in touch?” He hated how needy and pathetic he sounded to his own ears.

“Oh, yeah, sure, Cas. Of course. We can text and whatever. Eventually we can even hang out sometime, you know, once the heat’s off.” Cas felt sick, as he could hear the falsity in Dean’s voice. He sounded as though he hadn’t meant a word of what he’d just said.

“So…we did all this to get back at Sam and Jess, but…we aren’t eventually going to tell them that we weren’t together?” Cas asked, mostly for something to say that wasn’t what he was actually feeling right now. Like “don’t fucking leave” and “yes, Dean, I want to be dating for real” and “please don’t fucking make me do this.”

“Nah, them seeing us crash and burn is the lesson. Don’t meddle because it fucks up people’s lives, right?”

“I guess so. For what it’s worth, Dean –“

“Yeah, it was fun, right? All that plotting.” His voice still had that distant neutrality, but then it dipped into a flirtation that was patently affected. “And the sex wasn’t half bad, either, am I right?” He made a double clicking sound in his cheek – similar to the noise one called dogs with, Cas had always thought – and then he told Cas he had to go.

Cas slowly hung up and folded into a chair, lunch forgotten. Why was he such a coward? Why hadn’t he just told Dean, either when he’d asked or just now? He was losing Dean, anyway, was rejection so much worse?

“Tomorrow,” he told himself aloud. “When he comes to work and shuts us up in my office, I’m going to tell him,” he vowed to his coffee cup.

**Notes for the Chapter:**

> See? Cas knows he lied. I'm sure it will all be fine... ♥


	11. Fake date, Real Breakup

**Summary for the Chapter:**

> More lies lead to the truth.

**Notes for the Chapter:**

> Stupid boys are stupid.

By the time Monday arrived, Dean felt like there was an on/off switch inside him and someone else was controlling it by remote. He vacillated back and forth between an irrational anger – or worse, numbness – that made him want to sever all ties with Cas, and an intense desire to maintain his friendship with Cas at all costs.

It was closing in on noon now and Dean thought he’d better go ahead and send Cas a reminder text. He wasn’t sure which direction the switch was in right now, honestly, but he wasn’t sure how much more emotional flip-flopping he could take from himself at this point.

**You all set to go?**

**> Yes, I believe so. I’d like to get this over with. **

**Cool. And hey, for a bit of realism, I even went to the bar last night and picked up someone ;D**

Now why the fuck had he said _that_? The instant he hit send, he regretted having typed it. He _had_ gone to the bar, it was true, but he hadn’t gone home with anyone. Was he hoping to make Cas jealous? The guy wasn’t interested, so what was the point?

**> I see. I am to meet you in the front of the office at exactly one, correct?**

**Yeah and hey, I meant what I said about staying friends after, ok?**

It was a few minutes before he got a reply to that one and when he did, he felt like all the air had been taken out of the room.

**> Actually, I believe I would prefer it if we did not speak again after today. **

**> I will see you in just over half an hour. Goodbye, Dean.**

**What? Why?**

**Cas?**

**Dude, what the hell? I thought you wanted to stay friends, too?**

When his last three texts, sent several minutes apart, were ignored, Dean tried to call. Cas’ phone went straight to voicemail. He looked at the time. He had to go if he was going to make it there on time.

He rushed out to the car, and took off faster than was strictly legal. By the time he’d driven halfway to the office, he had worked himself into a state. Just what the fuck was Cas playing at? He wanted to be friends, he didn’t wanna be friends. He didn’t want the breakup, he wanted it as fast as possible.

This time the switch was flipped fully to angry and Dean didn’t think it was going to change until he got an explanation. When Dean got to the building where Sam, Jess, and Cas all worked, he ignored the elevator and took the stairs two at a time. He opened the heavy door from the hallway into the main office and glared around until he spotted Cas.

When Cas saw him, he looked like a deer in headlights. He was clearly unprepared for the very real fury that was currently on Dean’s face. He pointed and Cas, to his credit, aborted his flinch so that it was likely no one save Dean had noticed.

“You just turn off your phone and ignore me, with no explanation? Just goodbye and that’s it?” he asked in a voice every person close by could hear easily.

“Dean!” Cas hissed in a stage whisper. “Keep your voice down! Come to my office and we’ll talk about it."

“Do I need to call security?” the guy behind the counter asked, but Cas shook his head.

“No, Kevin, it’s fine. He’s not dangerous, just lacking in basic manners. I’ll be fine.”

Dean’s eyes narrowed at the manners comment and he stalked toward where Cas was walking. “Don’t think you’re getting out of answering the question,” he said without lowering his voice much. “I deserve an answer as to why you did a complete 180 on me.”

“Dean, can we save this for my office, please?” Cas asked as they rounded a corner.

“No!” Dean said sharply, grabbing Cas’ arm as he was stepping through the doorway. “I wanna know what the hell changed between yesterday and this afternoon that had you telling me we’re done and turning off your phone so we couldn’t even talk about it.”

Cas, who up to this point had maintained a calm exterior, suddenly snapped and got right into Dean’s face to whisper wildly, “What _changed_? You slept with someone else and you wanna know what _changed_?!”

At first Dean thought Cas had decided to follow their original script instead of having the real conversation. It took him out of himself for a moment, nonplussed. Then he realized that the bright spark he saw in Cas’ eyes wasn’t anger. It was hurt – and maybe the sheen of unshed tears. He glanced beyond Cas and saw that it was an office Cas had been stepping into.

“Come on,” he said in a quieter voice, gently ushering Cas through the door and closing it behind them. “Cas, what –“ He stopped and sighed, running his hands through his hair. “I asked you, remember? I asked you if you wanted this to be real.”

“Well, newsflash, Dean. I _lied_ , ok? I was scared and I lied.” Cas twisted his fingers in his own hair and pulled slightly. “Sam told me a long time ago that his brother lived his life from bedroom to bedroom. And when you asked me, that was all I could think about.” He closed his eyes and Dean’s chest ached when he saw that thick lower lip tremble. “And you proved me right, didn’t you?” Cas asked in a harsh whisper without opening his eyes.

“Cas, hey,” Dean said, but Cas didn’t open his eyes. A tear tracked down one of Cas’ cheeks and still he wouldn’t look at Dean. “Cas, I _didn’t_. I swear I didn’t. I don’t even know why I said that. I wanted…I don’t know, I wanted you to think I didn’t care any more than you did.” He stepped close and wrapped a hand around the side of Cas’ neck, swiping a thumb across his cheek. “Because I thought you didn’t, Cas. You told me –“

“How can I believe you?” Cas asked with his eyes still closed. “You said it happened before.” 

Dean sighed heavily and let his hand slip away from Cas’ face. “A long time ago, I really did have a big relationship panic. I went out, got so drunk that I blacked out, and the only reason I know I slept with someone is because they were in my bed the next morning, naked. I have never knowingly cheated on anyone.” He put his hand back on Cas’ face. “If I didn’t cheat before, I sure as hell wouldn’t start with you, Cas.” 

“Shit,” Cas swore shakily, before opening his eyes. He stared at Dean for a long moment before taking a deep breath. “I meant it when I said we shouldn’t break up. I lied when I said I didn’t want to date for real. Can we fix this?” he asked, his eyes pleading with Dean to say yes.

Dean, suddenly feeling like he could breathe again for the first time in days, smiled. “Yeah,” he told him, nodding. “Yeah, Cas. It’s not really broken, is it? I mean, we’re both kinda stupid and we need to work on being honest, but otherwise, I think we’re ok, right?”

“We both want this to be real? It’s not just me?”

Dean smiled wider. “It’s not just you, Cas. I’ve wanted it to be real for a while now.”

“Oh, Dean,” Cas said with a watery sigh.

He stepped forward into Dean’s arms and they hugged tightly for a long moment. They were interrupted by someone opening the door. They looked up at the same moment and saw Sam, his face furrowed in concern.

“Guys, what’s going on? I was on a call or I’d have come sooner –“

In unison, they pointed and said, “This is all your fault!”

**Notes for the Chapter:**

> Phew! Finally, the truth comes out. Dammit, Sammy. ♥


	12. The situation

**Summary for the Chapter:**

> Sam finds out the truth and Cas comes clean about his past.

**Notes for the Chapter:**

> Ok, folks, the ride is almost over, but there are some bumps left (but also some smut). Also, just want to warn you that the next chapter is an epilogue and it's shorter than the rest. 
> 
> **TW:** (Hover over the word spoilers for warnings) **SPOILERS**

Cas was still shaking when Sam burst in on them. His emotions had been running high with everything that had happened and he wasn’t able to just shut it down and switch gears so easily. He and Dean were still holding on to each other, though, and that helped.

They had turned on Sam as one and called him out, but Cas left it to Dean to explain their accusation.

“You could have just sat down and had dinner with us and we could have gone from there. Maybe we’d have hit it off, maybe not, but it wasn’t up to you to force us together, Sam.”

“Dean, what are you talking about?” Sam asked, even though his eyes said he knew.

“Oh, don’t play dumb, Sam. You and Jess and this whole set up with me and Cas. You faked a dinner to get us together and thought we’d be too stupid to see through it.” Sam opened and closed his mouth a couple of times, but said nothing. “So we hatched a little payback plot for you and Jess. Teach you a lesson, right?” Dean stepped away from Cas and scrubbed a rough hand back and forth over his hair. “Only, it didn’t quite work out, did it?” he asked quietly of no one in particular.

“Wait, what kind of plot?” Sam finally got out.

“We weren’t really dating, Sam,” Cas interjected before Dean could. “We devised a plan to pretend to date and then pretend to have a spectacular breakup, so that you would learn not to meddle in other people’s affairs.” Cas sighed and sank wearily in a nearby chair. “Only I ended up falling for your brother and screwing up telling him about it and it all became a big mess.”

“Hey!” Dean said sharply, coming forward to kneel in front of him. “Hey,” he said more softly, capturing his face in two gentle hands. “It’s not a mess now, remember? We’re good. It’s all good, right? We’re together. It’s gonna be fine, you hear me?”

Cas drew comfort from Dean’s touch and gaze and words. He didn’t know why he had gotten so worked up again. They _had_ decided it was fine. He nodded. Tried a smile. “Yes, you’re right. I’m sorry. Just emotional aftershocks, I suppose.”

Sam furrowed his brow and shook his head vigorously. “So, wait, you guys weren’t dating this whole time? But…now you are?”

“We started out not dating, Sam,” Dean explained. “But then somewhere along the line, we started dating without realizing it and we both acted stupid,” he said with a pointed look at Cas. “But then we had our big blow up and figured out what we both wanted, so now, yeah, we’re together for real.” Then his face hardened and he pointed at Sam. “And don’t you ever meddle in my life like this again, Sammy.”

“If you really thought that we would be so good together, then you should have trusted that just meeting each other would have been good enough. We aren’t children who need your scheming and machinations, Sam, really.”

Just then, Jess showed up in the doorway behind Sam. He turned to her and said, “This is your fault!” Cas and Dean shared a look and laughed. Then they closed Sam and Jess out and kissed for a long time.

Later that night, after a hot and heavy makeup make-out session, Dean took a moment away from scraping his teeth against Cas’ ear to whisper in a broken, needy voice, “Need to be inside you, Cas. Please?”

Cas made a noise of which he hadn’t previously realized he was capable. “Yes, Dean,” he growled as Dean’s mouth sucked at his neck. “Fuck me, please, want it so much.” It would be their first time having penetrative sex, but Cas wasn’t really worried. 

Once they moved into the bedroom, Cas felt a few moments of fear, but they were quickly soothed away by Dean’s tenderness. Rather than rushing to it, as he’d sounded like he wanted, Dean stopped and got them both worked up again with kissing and petting. When they were finally ready, Dean took his time prepping Cas, until Cas was incoherent with desire. 

His ass and cock both ached with the need for Dean to fill him up. Every nerve in his lower body was screaming Dean’s name already and begging shamelessly until the words were tumbling out of Cas’ own mouth. “Please, Dean, _please_ ,” he gasped out as three of those fingers brushed over that little ball of ecstasy that was his prostate yet again. 

“Shh, baby, it’s ok, I'm right here,” Dean whispered as he withdrew his fingers and gently turned Cas over before kissing him half-unconscious. 

Cas was so lost in the movement of Dean’s mouth that Dean’s head moving against his hole barely registered. Then it was slowly, slowly, sliding into him and bringing with it feelings Cas had never experienced before. Not that Dean wasn’t already good enough at that as it was. 

Dean was straddling one of Cas’ thighs and had the other pressed up until the knee was against Cas’ shoulder. It gave him perfect access to stroke Cas’ cock, slick as it was with precome on the head. 

Dean whispered filthy yet somehow sweet nothings and Cas babbled incoherently in phrases he’d never used before. Mindless sex talk like “right there” and “just like that” and “oh, God, yes, harder, fuck, Dean, more!” Then they were both coming, Cas uncertain who crested first or yelled loudest. 

As they lay in bed a short time later, Cas confessed, “It’s been more than eight years since I last did that.”

Dean startled and stared, as Cas had known that he would. “What? Why?” His eyes narrowed to slits. “Cas? What’s your real ‘situation’?”

Cas sighed. “You have to understand, I grew up in a very religious family. So I didn’t accept who I was until I was in college. That meant there was no teenage experimentation with sex at all. I was a virgin until I was 22.”

“You didn’t date at all,” Dean said and it wasn’t a question, but Cas answered anyway.

“No. And then I met Nathaniel. He had a similar background to my own, so I believed we had a lot in common. However, he was keen to make up for lost time and he pressured me constantly for sex.” He slid a hand down the sheet, enjoying the cool sensation against his skin.

“He forced you?” Dean asked in a horrified whisper.

Cas shook his head. “Not exactly. I finally agreed to it, but as I said, I had no practical experience. I knew nothing of prep or even the importance of proper lubrication.” He shook his head and laughed. “Vasoline and repetitions of the phrase ‘just relax, baby,’ that was my prep and lube for my first time. It was, as you can imagine, painful and awkward and not even a little bit sexy.” Cas bit his lip. “And he didn’t seem all that interested in the fact that I wasn’t enjoying it.”

“So you broke up and didn’t have sex again until just now?”

“Oh, I wish it were that simple, Dean. I kept doing it, hoping it would get better. That’s what they tell girls, right? The first time is bad, but it gets better? It’s not even true for them, but that’s the party line.” He sighed and reached for Dean’s hand to stroke it softly. “I made a friend, Balthazar, and talked to him about it. He opened my eyes to what was wrong.”

Dean’s arm came around to pet Cas’ back. “So then what happened?”

“Rather than assume the worst of this boy I loved, I tried to talk to him about it. I wanted to enjoy sex with him and I knew we could, if only we tried the things Balt had told me about.” Cas shook his head. “He didn’t care. He actually said to me that he was getting off, so what difference did it make? So I left him and closed myself off for a long time.”

“What made me different?” Dean asked quietly.

“Are you kidding? Everything. The level of attraction, for one thing. That’s completely new. And the level of pure gentleness that you showed me, even when you were going crazy with lust, you were still tender and never hurtful.”

Cas smiled genuinely and widely, though there were tears forming in his eyes. “Do you have any idea how much it meant that you didn’t try to have anal sex right away? You didn’t really know what had happened to me, but somehow I got the impression you were taking it slow on purpose.”  He searched Dean’s face. “You were, weren’t you?” he asked in wonder.

Dean stared at their joined hands. “I could see something in your eyes that night. You were scared. Not of me, though, I could tell. And I just didn’t want to hurt you. I knew your last time had been bad, whatever the story was, and I just wanted you to feel good.” Then Dean’s head snapped up. “So those were, like, your first orgasms with another person?”

Cas smiled again. “Yes, Dean. And they were amazing.”

Dean’s smile turned feral. “I think we need to make up for lost time.” They didn’t talk again for a long time.

**Notes for the Chapter:**

> Yes, I think Cas needs many more orgasms, Dean. Get on that. ♥  
> (Just as an aside, in the original version of this chapter, the line about penetrative sex was the only reference to them having sex. However, as no fewer than 4 of you basically said you'd only forgive me for pain if there was more smut, I wrote the bonus sex scene you have just read on this, the night before the schedule post of this chapter. You're welcome - now be sure and give me some love! ;D) ♥


	13. Epilogue

**Summary for the Chapter:**

> Sam and Jess have a barbecue.

**Notes for the Chapter:**

> Short and sweet, this last one.

**_4 months later_ **

“Think we should let him off the hook anytime soon?” Cas asked as he bit into his third mini burger. They were standing off by the corner of the house, watching Sam and Jess’ latest barbecue go on around them.

Dean swallowed the last of his fourth slider and shook his head. He washed it all down with beer and said, “If I’ve learned anything as an older brother, it’s the fact that there are things you don’t let go too easily.” He grinned. “Especially when it’s so much fun to watch him squirm.”

Cas laughed. “That is true. Should we maybe give Jess a pass, given that she’s with child?”

“Hell no! She can’t yell at me for trying to help her carry shit and then expect special treatment when it comes to this. Besides, it’ll teach her not to try this crap on my niece.”

“Or nephew,” Cas reminded him yet again.

“Yeah, I want it to be a girl, though,” Dean admitted, shrugging.

“Why is that, again?” Cas asked, honestly curious.

“I raised a little brother. I never had a sister, though. I think it might be cool to have a little girl around, you know?” He popped a potato wedge in his mouth and offered Cas another beer.

“Thank you.” Cas gave him a look that Dean knew meant he was about to confess something he was shy about, so he perked up. “You know, if I’m honest, I’m not really upset at either of them anymore.”

“No?”

Cas shook his head. “They should have done it differently and just had a dinner with all four of us, but…if they hadn’t done anything at all…” He glanced up at Dean through his lashes in the way he knew drove Dean absolutely crazy.

Dean eyed him hungrily. “If you’re trying to have an emotional moment, it might not be the best time to pull the bedroom eyes on me, you know. Especially since there are children present,” he said, stepping well inside Cas’ personal space.

“They have a guest room. And I can express my emotions without words, you know,” Cas said in a husky voice Dean could feel in his chest.

“Fuck, how can you still get me this worked up? Isn’t the honeymoon supposed to be over by now?” Dean growled, pulling Cas in for a chaste but firm kiss.

“How should I know? I have literally no prior relationship experience.”

“Yeah, well, me neither. I do know it’s our 6 month anniversary, though,” Dean whispered in Cas’ ear.

“Is it?” Cas asked breathlessly as Dean nuzzled Cas’ ear with his nose.

“Mm-hm. So I think I should give you whatever you want,” he said, running a hand down his boyfriend’s back teasingly.

“I want you to take me home and fuck me stupid,” Cas said, seriously.

“You got it,” Dean said with a grin as he turned to head toward where he’d parked the car. “Oh, and Cas?” he called over his shoulder once they were out of sight of everyone else. “I’m not mad at them, either.”

Cas’ bright smile reminded him why all the painful parts had been worth it. “Oh, no?”

“Nope. Best favor my brother ever did me,” he said, eyes soft on Cas’ face.

“Take me home and fuck me, stupid,” Cas whispered as he caught up.

“Anything you say, gorgeous,” Dean promised, then kissed Cas thoroughly and took him home.

**Notes for the Chapter:**

> This is the end, may darlings. I do hope you've enjoyed it.  
> You've forgiven me for that whole pain thing, right?  
> ...  
> Hello?  
> ...Hello?  
> (♥)

**Author's Note:**

> Talk to me darlings. How did I do? ♥  
> Follow my [author Tumblr](http://jamiedeanwrites.tumblr.com//post/118453611081/the-story-of-jax-and-dylan) for boys kissing, pansexual facts, book news and general shenanigans.


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